PL327901A1 - Novel crystalline form of n-(4-trifluoromethylphenyl)-5-methylisoxazol-4-carboxamide, method of obtaining crystalline form of that compound, pharmaceutic agent, application of such novel crystalline form and method of obtaining such pharmaceutic agent - Google Patents
Novel crystalline form of n-(4-trifluoromethylphenyl)-5-methylisoxazol-4-carboxamide, method of obtaining crystalline form of that compound, pharmaceutic agent, application of such novel crystalline form and method of obtaining such pharmaceutic agentInfo
- Publication number
- PL327901A1 PL327901A1 PL98327901A PL32790198A PL327901A1 PL 327901 A1 PL327901 A1 PL 327901A1 PL 98327901 A PL98327901 A PL 98327901A PL 32790198 A PL32790198 A PL 32790198A PL 327901 A1 PL327901 A1 PL 327901A1
- Authority
- PL
- Poland
- Prior art keywords
- crystalline form
- obtaining
- trifluoromethylphenyl
- carboxamide
- compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 239000013078 crystal Substances 0.000 abstract 5
- 238000012986 modification Methods 0.000 abstract 5
- 230000004048 modification Effects 0.000 abstract 5
- VHOGYURTWQBHIL-UHFFFAOYSA-N leflunomide Chemical compound O1N=CC(C(=O)NC=2C=CC(=CC=2)C(F)(F)F)=C1C VHOGYURTWQBHIL-UHFFFAOYSA-N 0.000 abstract 3
- 238000002441 X-ray diffraction Methods 0.000 abstract 2
- 230000005540 biological transmission Effects 0.000 abstract 1
- 230000005855 radiation Effects 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Ophthalmology & Optometry (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Oncology (AREA)
- Biomedical Technology (AREA)
- Communicable Diseases (AREA)
- Neurosurgery (AREA)
- Reproductive Health (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Crystal modification 2 of N-(4-trifluoromethylphenyl)-5-met hylisoxazole-4-carboxamide (I) (leflunomid; HWA 486) is new. - New crystal modification 2 of N-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamide (I) has lines (diffraction angles 2theta ([deg])) of strong intensity at 10.65, 14.20, 14.80, 16.10, 21.70, 23.15, 24.40, 24.85, 25.50, 25.85, 26.90 and 29.85 and of medium intensity at 7.40, 9.80, 13.10, 15.45, 16.80, 20.70, 21.45, 22.80, 23.85, 27.25 and 28.95 in the X-ray diffraction graph using Cu-Kalpha 1 radiation in the focusing Deybe-Scherrer procedure and transmission. Compound (I) is known from US 4284786. Independent claims are included for: (A) the preparation of crystal modification 2; and (B) the preparation of crystal modification 1 of compound (I) having lines of strong intensity at 16.70, 18.90, 23.00, 23.65 and 2.05 and lines of medium intensity at 8.35, 12.65, 15.00, 15.30, 18.35, 21.55, 24.10, 24.65, 25.45, 26.65, 27.40, 28.00 and 28.30 in the X-ray diffraction graph measured and defined in the same manner as for crystal modification 2. -
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19734438A DE19734438A1 (en) | 1997-08-08 | 1997-08-08 | New crystal modification 2 of leflunomid has better water solubility than modification 1 and is stable over wide temperature range |
| DE1997156093 DE19756093A1 (en) | 1997-12-17 | 1997-12-17 | New crystal modification 2 of leflunomid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL327901A1 true PL327901A1 (en) | 1999-02-15 |
| PL192126B1 PL192126B1 (en) | 2006-09-29 |
Family
ID=26038983
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL327901A PL192126B1 (en) | 1997-08-08 | 1998-08-07 | Novel crystalline form of n-(4-trifluoromethylphenyl)-5-methylisoxazol-4-carboxamide, method of obtaining crystalline form of that compound, pharmaceutic agent, application of such novel crystalline form and method of obtaining such pharmaceutic agent |
Country Status (28)
| Country | Link |
|---|---|
| US (5) | US6060494A (en) |
| EP (2) | EP0903345B1 (en) |
| JP (2) | JPH11124372A (en) |
| KR (2) | KR100544041B1 (en) |
| CN (2) | CN1089759C (en) |
| AR (1) | AR015418A1 (en) |
| AT (2) | ATE207065T1 (en) |
| AU (1) | AU752764B2 (en) |
| BR (1) | BR9806568A (en) |
| CA (1) | CA2245267C (en) |
| CZ (3) | CZ292943B6 (en) |
| DE (2) | DE59801792D1 (en) |
| DK (2) | DK0903345T3 (en) |
| ES (2) | ES2166205T3 (en) |
| GR (1) | GR3034814T3 (en) |
| HK (2) | HK1017681A1 (en) |
| HU (2) | HU229232B1 (en) |
| ID (1) | ID20667A (en) |
| IL (1) | IL125671A (en) |
| NO (1) | NO310871B1 (en) |
| NZ (1) | NZ331270A (en) |
| PL (1) | PL192126B1 (en) |
| PT (2) | PT903345E (en) |
| RU (1) | RU2224753C2 (en) |
| SK (2) | SK285216B6 (en) |
| TR (2) | TR200600582A1 (en) |
| TW (1) | TW593288B (en) |
| UA (1) | UA54411C2 (en) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0903345B1 (en) * | 1997-08-08 | 2000-10-04 | Aventis Pharma Deutschland GmbH | Crystal form of N-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamid |
| DE19908527C2 (en) | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Process for the crystallization of N- (4-trifluoromethylphenyl) -5-methyl-isoxazole-4-carboxamide |
| AU779931B2 (en) * | 1999-12-16 | 2005-02-17 | Teva Pharmaceutical Industries Ltd. | Novel processes for making- and a new crystalline form of- leflunomide |
| ES2237553T3 (en) * | 2000-02-15 | 2005-08-01 | Teva Pharmaceutical Industries Ltd. | PROCEDURE FOR THE SYNTHESIS OF LEFLUNOMIDE. |
| WO2002040458A1 (en) * | 2000-11-17 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Isoxazole derivatives |
| GB0123571D0 (en) | 2001-04-05 | 2001-11-21 | Aventis Pharm Prod Inc | Use of (Z)-2-cyano-3-hydroxy-but-2-enoic acid-(4'-trifluoromethylphenyl)-amide for treating multiple sclerosis |
| US7429593B2 (en) | 2001-09-14 | 2008-09-30 | Shionogi & Co., Ltd. | Utilities of amide compounds |
| WO2003068239A1 (en) * | 2002-02-12 | 2003-08-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel drugs for external use |
| US20050158371A1 (en) * | 2002-02-12 | 2005-07-21 | Sumitomo Pharmaceuticals Co., Ltd. | Novel external agent |
| ES2232332T3 (en) * | 2003-03-12 | 2007-08-16 | Teva Pharmaceutical Industries Ltd | STAL PHARMACEUTICAL COMPOSITIONS OF DESLORATADINA. |
| US20060135547A1 (en) * | 2003-03-12 | 2006-06-22 | Toth Zoltan G | Stable pharmaceutical compositions of desloratadine and processes for preparation of polymorphic forms of desloratadine |
| JP4223428B2 (en) * | 2004-03-31 | 2009-02-12 | 富士通メディアデバイス株式会社 | Filter and manufacturing method thereof |
| WO2007067710A1 (en) * | 2005-12-08 | 2007-06-14 | Amphora Discovery Corporation | Certain chemical entities, compositions, and methods for modulating trpv1 |
| CN101143834B (en) * | 2006-09-15 | 2010-09-08 | 欣凯医药化工中间体（上海）有限公司 | Polymorphism for N-(4-trifluoromethylphenyl)-2-cyano-3-hydroxycrotonamide sodium salt and preparation method thereof |
| UY31695A (en) * | 2008-03-10 | 2009-11-10 | Takeda Pharmaceutical | BENCIMIDAZOL COMPOSITE CRYSTAL |
| CN104666238B (en) | 2009-09-18 | 2018-04-06 | 赛诺菲 | 3 hydroxyl fourth of stability-enhanced (Z) 2 cyano group 2 olefin(e) acid (4 ' trifluoromethyl) acid amides tablet formulation |
| CN103977594B (en) * | 2014-06-03 | 2016-02-17 | 江苏九九久科技股份有限公司 | A kind of method for crystallising |
| US9895370B2 (en) * | 2015-11-19 | 2018-02-20 | Pharmedix.Co., Ltd | Pharmaceutical composition for preventing or treating of cirrhosis of liver comprising G protein coupled receptor 119 ligand as an active ingredient |
| CN109180599A (en) * | 2018-09-03 | 2019-01-11 | 深圳市新阳唯康科技有限公司 | A kind of leflunomide crystal compound and preparation method thereof |
| CN112898215B (en) * | 2021-02-04 | 2022-11-08 | 美罗药业股份有限公司 | Preparation method of leflunomide crystal form I |
| CN114716388B (en) * | 2021-11-04 | 2024-02-13 | 江苏冠军科技集团股份有限公司 | Sulfonamide-silver compound and preparation method thereof |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2524959C2 (en) * | 1975-06-05 | 1983-02-10 | Hoechst Ag, 6000 Frankfurt | 5-methyl-isoxazole-4-carboxylic acid anilides, process for their preparation, agents containing these compounds |
| NL186239B (en) * | 1975-06-05 | Hoechst Ag | PROCESS FOR THE PREPARATION OF A MEDICINAL PRODUCT WITH ANTIFLOGISTICAL AND / OR ANALGETICAL ACTION AND PROCEDURE FOR THE PREPARATION OF A 2-HYDROXYETHYLIDE ENCYANAACETIC ANILIDE SUITABLE FOR USE IN THIS PROCESS. | |
| ES448386A1 (en) * | 1975-06-05 | 1978-04-16 | Hoechst Ag | 5-Methyl-isoxazole-4-carboxylic acid anilides |
| DE2525959A1 (en) * | 1975-06-11 | 1977-02-10 | Focke Pfuhl Verpack Automat | PACKAGING FOR CIGARETTES, CIGARILLOS ETC. |
| DE2854439A1 (en) * | 1978-12-16 | 1980-07-03 | Hoechst Ag | AN ISOXAZOLE DERIVATIVE, METHOD FOR THE PRODUCTION THEREOF, AGENT AND USE THEREOF |
| IL63968A (en) * | 1980-10-01 | 1985-10-31 | Glaxo Group Ltd | Form 2 ranitidine hydrochloride,its preparation and pharmaceutical compositions containing it |
| US4935434A (en) * | 1988-01-26 | 1990-06-19 | Bristol-Myers Company | Antiarthritic isoxazole-4-carboxamides |
| US5583150A (en) * | 1989-08-18 | 1996-12-10 | Alcon Laboratories, Inc. | 5-methyl-isoxazole-4-carboxylic acid anilides and 2-hydroxyethylidene-cyano acetic anilides for the treatment of ocular diseases |
| DK0527736T3 (en) * | 1990-05-18 | 1997-10-20 | Hoechst Ag | Isoxazole-4-carboxylic acid amides and hydroxyalkylidene-cyanoacetamides, drugs containing these compounds and the use of these drugs. |
| DE4127737A1 (en) * | 1991-08-22 | 1993-02-25 | Hoechst Ag | MEDICINAL PRODUCTS FOR TREATMENT OF REPELLATION REACTIONS IN ORGAN PLANTING |
| GB9209330D0 (en) * | 1992-04-30 | 1992-06-17 | Roussel Lab Ltd | Chemical compounds |
| ES2124800T3 (en) * | 1993-01-08 | 1999-02-16 | Hoechst Ag | USE OF LEFLUNOMIDE FOR INTERLEUKIN 1 BETA INHIBITION. |
| ATE174219T1 (en) * | 1993-01-08 | 1998-12-15 | Hoechst Ag | USE OF LEFLUNOMIDE TO INHIBIT TUMOR NECROSIS FACTOR ALPHA |
| ATE174220T1 (en) * | 1993-01-08 | 1998-12-15 | Hoechst Ag | USE OF LEFLUNOMIDE TO INHIBIT INTERLEUKIN 8 |
| TW314467B (en) * | 1993-03-31 | 1997-09-01 | Hoechst Ag | |
| GB9320299D0 (en) * | 1993-10-01 | 1993-11-17 | Roussel Lab Ltd | Isoxazole derivatives |
| US5610173A (en) * | 1994-01-07 | 1997-03-11 | Sugen, Inc. | Formulations for lipophilic compounds |
| ATE194912T1 (en) * | 1994-10-17 | 2000-08-15 | Aventis Pharma Ltd | AGENTS FOR THE PREVENTION AND CURE OF TYPE I ALLERGIC DISEASES |
| AR001982A1 (en) * | 1995-02-06 | 1998-01-07 | Smithkline Beecham Plc | PAROXETINE CHLORHYDRATE ANHYDRATED, AND PROCEDURE FOR ITS PREPARATION |
| DE19539638A1 (en) * | 1995-10-25 | 1997-04-30 | Hoechst Ag | The use of isoxazole and crotonic acid amide derivatives for the treatment of cancer |
| US6316479B1 (en) * | 1997-05-19 | 2001-11-13 | Sugen, Inc. | Isoxazole-4-carboxamide compounds active against protein tryosine kinase related disorders |
| HRP980291A2 (en) * | 1997-06-16 | 1999-04-30 | Lin-Hua Zhang | Crystalline roxifiban |
| EP0903345B1 (en) * | 1997-08-08 | 2000-10-04 | Aventis Pharma Deutschland GmbH | Crystal form of N-(4-trifluoromethylphenyl)-5-methylisoxazole-4-carboxamid |
| US6096770A (en) * | 1998-08-03 | 2000-08-01 | American Home Products Corporation | Anthranilic acid analogs |
| DE19908527C2 (en) * | 1999-02-26 | 2001-08-30 | Aventis Pharma Gmbh | Process for the crystallization of N- (4-trifluoromethylphenyl) -5-methyl-isoxazole-4-carboxamide |
| AU779931B2 (en) * | 1999-12-16 | 2005-02-17 | Teva Pharmaceutical Industries Ltd. | Novel processes for making- and a new crystalline form of- leflunomide |
| ES2237553T3 (en) * | 2000-02-15 | 2005-08-01 | Teva Pharmaceutical Industries Ltd. | PROCEDURE FOR THE SYNTHESIS OF LEFLUNOMIDE. |
| US6727272B1 (en) * | 2002-07-15 | 2004-04-27 | Unitech Pharmaceuticals, Inc. | Leflunomide analogs for treating rheumatoid arthritis |
-
1998
- 1998-07-31 EP EP98114373A patent/EP0903345B1/en not_active Expired - Lifetime
- 1998-07-31 AT AT99117098T patent/ATE207065T1/en active
- 1998-07-31 PT PT98114373T patent/PT903345E/en unknown
- 1998-07-31 ES ES99117098T patent/ES2166205T3/en not_active Expired - Lifetime
- 1998-07-31 DK DK98114373T patent/DK0903345T3/en active
- 1998-07-31 DE DE59801792T patent/DE59801792D1/en not_active Expired - Lifetime
- 1998-07-31 PT PT99117098T patent/PT987256E/en unknown
- 1998-07-31 ES ES98114373T patent/ES2150808T3/en not_active Expired - Lifetime
- 1998-07-31 EP EP99117098A patent/EP0987256B1/en not_active Expired - Lifetime
- 1998-07-31 DE DE59800287T patent/DE59800287D1/en not_active Expired - Lifetime
- 1998-07-31 AT AT98114373T patent/ATE196764T1/en active
- 1998-07-31 DK DK99117098T patent/DK0987256T3/en active
- 1998-08-05 CZ CZ19982468A patent/CZ292943B6/en not_active IP Right Cessation
- 1998-08-05 IL IL12567198A patent/IL125671A/en not_active IP Right Cessation
- 1998-08-05 CZ CZ20032982A patent/CZ301514B6/en not_active IP Right Cessation
- 1998-08-05 CZ CZ20032983A patent/CZ301426B6/en not_active IP Right Cessation
- 1998-08-06 UA UA98084307A patent/UA54411C2/en unknown
- 1998-08-06 TW TW087112927A patent/TW593288B/en not_active IP Right Cessation
- 1998-08-06 US US09/129,783 patent/US6060494A/en not_active Expired - Lifetime
- 1998-08-06 AR ARP980103900A patent/AR015418A1/en active IP Right Grant
- 1998-08-06 NZ NZ331270A patent/NZ331270A/en not_active IP Right Cessation
- 1998-08-06 TR TR2006/00582A patent/TR200600582A1/en unknown
- 1998-08-06 SK SK1521-2001A patent/SK285216B6/en not_active IP Right Cessation
- 1998-08-06 SK SK1058-98A patent/SK282641B6/en not_active IP Right Cessation
- 1998-08-06 TR TR1998/01513A patent/TR199801513A3/en unknown
- 1998-08-06 ID IDP981098A patent/ID20667A/en unknown
- 1998-08-07 JP JP10224015A patent/JPH11124372A/en active Pending
- 1998-08-07 HU HU0700190A patent/HU229232B1/en unknown
- 1998-08-07 CA CA002245267A patent/CA2245267C/en not_active Expired - Lifetime
- 1998-08-07 AU AU78870/98A patent/AU752764B2/en not_active Expired
- 1998-08-07 BR BR9806568-8A patent/BR9806568A/en not_active Application Discontinuation
- 1998-08-07 CN CN98116235A patent/CN1089759C/en not_active Expired - Lifetime
- 1998-08-07 KR KR1019980032110A patent/KR100544041B1/en not_active IP Right Cessation
- 1998-08-07 HU HU9801844A patent/HU225870B1/en unknown
- 1998-08-07 RU RU98115390/04A patent/RU2224753C2/en active
- 1998-08-07 CN CNB021045747A patent/CN1181064C/en not_active Expired - Lifetime
- 1998-08-07 NO NO19983632A patent/NO310871B1/en not_active IP Right Cessation
- 1998-08-07 PL PL327901A patent/PL192126B1/en unknown
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1999
- 1999-06-30 HK HK99102767A patent/HK1017681A1/en not_active IP Right Cessation
- 1999-10-28 US US09/428,499 patent/US6221891B1/en not_active Expired - Lifetime
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2000
- 2000-11-10 GR GR20000402501T patent/GR3034814T3/en unknown
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2001
- 2001-01-19 US US09/764,258 patent/US6552202B2/en not_active Expired - Lifetime
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2002
- 2002-11-25 US US10/302,872 patent/US6900334B2/en not_active Expired - Lifetime
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2003
- 2003-02-19 HK HK03101247.6A patent/HK1049481B/en not_active IP Right Cessation
-
2004
- 2004-04-23 US US10/830,307 patent/US6995272B2/en not_active Expired - Lifetime
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2005
- 2005-06-28 KR KR1020050056044A patent/KR100588254B1/en not_active IP Right Cessation
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2009
- 2009-07-28 JP JP2009175137A patent/JP2009280604A/en active Pending
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